


Love at First Sight

by MermaidMarie



Category: Supergirl (TV 2015)
Genre: Alternate Universe - Canon Divergence, Canon Rewrite, Eventual Jimmy Olsen/Winn Schott Jr., Kara Danvers & Winn Schott Jr. Friendship, M/M, Slow Build, Slow Burn
Language: English
Status: In-Progress
Published: 2017-05-07
Updated: 2017-07-10
Packaged: 2018-10-29 06:12:39
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,235
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10848105
Author URL: https://archiveofourown.org/users/MermaidMarie/pseuds/MermaidMarie
Summary: In which Winn Schott isn't prepared when he first sees the new guy at CatCo.





	1. Chapter 1

**Author's Note:**

> What am I even doing? I think I'm just rewriting Supergirl starting from the pilot, except from Winn's perspective, and he is bi like he was always supposed to be anyway. We'll see how far I go with this. I might be skipping episodes or switching some around because, well, no one can stop me. 
> 
> Let me know what you think!

             Today was the day. Winn was going to finally gather up the courage to ask Kara on a date. He’d been pining for her for long enough. It was becoming a pattern for him to just become close friends with someone he had feelings for, because he could never manage to ask them out. Rejection was too scary.

             But it was time to finally try. Wasn’t it?

             Kara was putting her stuff down on the desk, her ponytail swinging. Winn could almost feel himself getting tongue-tied already. She was just so _pretty._ But it was as good a time as any. “Hey, um, I was wondering if you maybe wanna…” Winn started. Kara turned back to look at him and he tried not to stutter. “I don’t know, go see- go see a movie tonight.”

             “I can’t, I’m sorry,” Kara replied, wide-eyed. She inhaled sharply and smiled. “I have a date.”

             Great, so it seemed like she didn’t even realize Winn was asking her out. Go figure. Winn decided for about the tenth time that he really needed to stop getting crushes on people who were way out of his league. “A date. Really,” Winn said, barely able to mask his disappointment. It was a good thing Kara was so unbelievably oblivious. “That’s great… Fun. Dating is fun. Who is that with?” _And how much better than me are they?_

             “It’s an online date,” Kara replied, settling down at her desk. So she was rejecting him for someone she hadn’t even met yet. Winn’s ego was small enough already without this extra bruising. “Says we are 82% compatible, so. Should be good.”

             “You know that you can’t quantify emotions based on an algorithm?” Winn replied. He knew perfectly well that feelings weren’t that easy.

             “Winn, you’re IT, isn’t your whole life based on algorithms?” Kara said.

             “Yes, so if there was an algorithm for love, I think that I would know about it,” Winn replied. If only. “Just like you’re gonna know when it hits you, Kara. It’ll be all… _Wah-pow._ ” Winn was pretty sure that was how it worked when he first saw Kara, anyway. It just hit him when their eyes met. Clearly, love at first sight didn’t always go both ways.

             That’s when the boss, Cat, got there, and Winn knew he wouldn’t be seeing much of Kara for the rest of the day. He tried to just keep his focus on his work on the computer, desperately trying not to replay the morning in his mind. He’d spent this long working up the courage to ask her out, and she didn’t even realize he was doing it. She was only ever going to see him as a friend. He’d have to get a handle on his feelings if he wanted to keep hanging out with her.

             Which, of course, he did. She was beautiful and funny and smart. Dating her would’ve been amazing, but being friends with her was amazing, too. It’s not like Winn’s pride was hurt any more than usual, anyway.

             The next day at work, the place was buzzing with excitement over the woman who’d flown and rescued the plane. Everyone had something to say about it. Winn was still a little bitter that Metropolis got to have Superman, so he couldn’t find it in him to be especially excited or impressed. But it was nice to have something interesting shake up the office at least.

             Kara was in Cat’s office, along with a bunch of other employees, presumably discussing what they were going to do with the story of the flying woman. Winn, though he’d promised himself he was going to try and get rid of his crush on Kara, couldn’t help glancing over at the door every few seconds. Waiting for her to come back. It was a little pathetic, sure, but pining always was, so Winn was used to it.

             Finally, he saw her come through the doorway, and he was about to pretend to not have noticed and stare back at his computer when he saw him. The man that Kara was walking with.

             And Winn couldn’t pull his eyes away. He figured he probably looked like a cartoon character, with his mouth hanging open and animated hearts circling his head. This guy was new. Winn would’ve remembered seeing him before.

             He was tall, broad shouldered with his head held high. He walked like a prince, long, certain strides with his hands in his pockets. And that _smile._ Winn could feel himself melting with how warm and radiant that smile was. He had kind eyes, and a confident glow. So much for not getting crushes on people that were out of Winn’s league. He was hopeless now.

             If he’d thought that seeing Kara for the first time had hit him… Well, he just wasn’t prepared for this at all. He could hardly breathe.

_Wah-pow._


	2. Chapter 2

**Summary for the Chapter:**

> Taking place during Supergirl 1.01.

**Notes for the Chapter:**

> How long is this story gonna be? Good question. I have no answers. I'm just avoiding my responsibilities and I really like Winn Schott.

              Winn didn’t have a chance to go try to casually meet the new guy, by _"accidentally"_ running into him and then just trying to act nonchalant. _Oh, are you new here? Cool, cool, welcome. Let me know if you need any help or anything, and, oh, also, by the way, you’re ridiculously attractive and I think you’re my soul mate. Thought you should know._

              It was probably for the best, because Winn never actually succeeded in his plans to seem casual around his crushes. He always ended up tongue-tied and fawning, and then they just thought that he was awkward and fumbling in general. Which, of course, he was, but that didn’t mean they needed to know that.

              In any case, Winn was too caught up in the fact that his best friend was an _alien_ and he didn’t even _know._  He didn't have much time to worry much about the new guy at work. He had been dreaming of being friends with a superhero since he became such a fan of Superman.

              It didn’t exactly help him get over his unrequited crush on her, though, and move on to his _new_ probably still unrequited crush on a complete stranger. It made it all the more difficult, really. Because not only was she beautiful, smart, and kind, she was also brave and heroic and _she could literally fly._

              She also told _him_ about it, which Winn felt like had to mean something. She let him in on her biggest secret. She let him _help._

              At least his sewing skills from his time doing costumes for the theater department in high school were finally becoming useful. And his dreams of being a character in a comic book were coming true, too.

              “Where’s my cape?” Kara asked as she tried on the first iteration of Winn’s costume design.

              “Capes are _lame,_ ” he replied. “And you can tell your cousin I said so.” He paused. “Actually, never- never do that.” Not that he was afraid of Superman. He just really, really wanted to be friends with him, and now it was actually a realistic possibility.

              Winn was at Kara’s place basically all night, trying to figure out a costume for Kara. They managed to get it right in the fourth iteration. Winn stood up when Kara came out in it, a little breathless.

              “Kara, you look really pretty without your glasses,” he said, barely thinking about it. He was just about ready to melt. It was a _really_ good thing that Kara was so oblivious.

              “Winn,” she prompted, with a raised eyebrow.

              “So, uh,” Winn replied, shaken out of his daze and sitting back down. “To be a superhero, you need a crime.”

              So Winn hacked the NCPD and gave Kara locations, and Kara flew- _flew-_ off to go fight crime. It was pretty much everything Winn had dreamed as a kid. And also as an adult, if he was being honest. Being a part of a superhero team was exactly what made Winn feel important. Not to mention let him feel like he could move on from his past.

              Winn tweaked the costume as problems came up, as Kara learned more about the extent of her powers. _This could work,_ Winn thought. Kara wasn’t making the crush any easier, but at least it was getting his mind of the guy from work.

              He wondered what it would be like to _not_ fall in love with friends and strangers all the time. He imagined he’d have a lot more time on his hands. Imagine what he could get done if he just had that kind of energy and time leftover.

 ---

              At CatCo, Kara learned she’d been dubbed _Supergirl,_ seeming less than thrilled about it. Winn watched as she walked quickly into Cat’s office, almost wincing at the idea of confronting Cat Grant. He would certainly never want to do that. Cat was scary. 

              He sat at his desk, waiting for Kara to come back out, glancing up a few times to see her pacing or gesturing frantically with her arms. He was finding it hard to concentrate on work.

              It only got worse when the tall, beautiful man walked past his desk and into Cat’s office. The two people Winn was in love with in the same room. He wondered if he’d ever be able to talk again.

              Maybe he should hold off on saying he’s _in love with_ the new guy until he’s at least learned his name, Winn thought to himself. But practicality and logic never seemed to win against heart and emotion for him, and Winn _did_ believe in love at first sight. He liked to believe he’d recognize it when it happened.

              His heart started pounding as Kara and Ridiculously Handsome Guy walked out of Cat’s office together.

              “I was handling the situation,” Kara was saying as they walked past Winn’s desk.

              “Oh, yeah? What was your plan?” Ridiculously Handsome Guy replied. _Even his voice is great,_ Winn thought to himself, melting.

              Neither of them looked at Winn, and they walked out of earshot and his line of sight. And Winn tried to pull himself together. There were just too many beautiful people in this world, he decided. It was unfair. How was he ever supposed to concentrate on anything, with all these people around him? He vaguely considered quitting his job at CatCo and getting a job where he would never have to look at anyone.

              The day crawled by, and he didn’t see Kara or the new guy at all for the rest of it. By the time the work day had ended, Winn was exhausted. He rushed back to his apartment as fast as he could, trying to avoid interacting with anyone. He just wanted to get home and relax.

              It had never taken much for Winn to acquire crushes on people. Ever since he was a teenager. He had crushes on his beautiful, intelligent friends, like Kara. Or on particularly attractive strangers, like the new guy at work. Or on various people who were just a little bit nice to him, like the barista who drew a smiley face on his coffee cup or the pretty girls who apologized and smiled after bumping into him on the street or the cute boys who would hold the door open and laugh when Winn stumbled over a thank you.

              His crushes were never returned. Or at least, that’s what he assumed since he never actually _told_ any of them how he felt. Or ever asked anyone out, really. He’d just become friends with them or admire them from afar. Being a shy romantic had some serious drawbacks.

 ---

              At CatCo the next day, Winn waited near the door until Kara came by.

              “If I believe the comments on the website,” he said, falling into place walking beside her. “They mentioned a _female/reptilian boxing match in the desert.”_

              Kara smiled. “I’ll tell you all about it at our next crime-fighting lunch hour.”

              Winn liked the sound of that. “Wait, so the Superfriends are back?”

              “We’re not calling ourselves that.”

              Winn walked as Kara walked away, smiling to himself. Maybe he’d never get over Kara. And maybe he’d never get the courage to talk to the Ridiculously Handsome Guy. But he was friends with a superhero and he was helping her fight crime, and fulfilling his childhood dreams was pretty exciting already.


	3. Chapter 3

**Summary for the Chapter:**

> Supergirl 1.02.

**Notes for the Chapter:**

> I wish my update schedule was less erratic. I'm sorry to anyone who might be following this story. I know. I have no excuse.

              Winn was running a little bit later to work than usual, trying to weave through to crowded sidewalk to get to the CatCo building. He mumbled apologies to the strangers he bumped into, trying not to make any eye contact. His whole life had gotten way more exciting in the past week, so he wasn’t sleeping quite as much.

              He finally got to the building, rushing through to the elevator when he saw the Ridiculously Handsome Guy waiting, hitting the button to go up.

              Winn’s heart started pounding and he immediately rushed to duck behind the corner. He held his breath until he heard the bell indicate the elevator’s arrival. He waited another several seconds to make sure that the elevator was gone.

              He was being _so ridiculous._ Hiding from his attractive coworker? Hadn’t he been trying to find a way to fabricate accidentally running into the guy so he could introduce himself? That would've been  _actually_ running into him accidentally.  _Oh, hi, you're the new guy, right? Welcome to CatCo, also I might be in love with you._

              _Stupid,_ he thought to himself as he took the next elevator by himself. Then again, he just wasn’t ready to try talking to the new guy yet. He never would’ve been able to get a real sentence out with no preparation first. He had to try to script the introduction, or he would just stutter. 

              He hung out by the elevator on his floor, as usual, until Kara came out with her head ducked.

              “Oh, God, is that smell you?” he asked, falling into step beside her.

              “Three showers and I still reek of burning oil,” she replied, glancing around to make sure no one could hear. “I went from superhero to eco-terrorist in a single bound.” Her voice was tense as she walked briskly.

              “Hey, hey,” Winn said kindly, jogging a little to keep up with her. “You’re just, like, a week into this superhero thing. You’re gonna make some mistakes.” He smiled as they got to their respective desks. She was so cute that he almost forgot about the new guy for a second.

              She turned up to look at the news playing on the TV, and Maxwell Lord was telling a reporter about the kind of trouble Supergirl would bring to National City. Winn glanced at Kara, noticing how disheartened she was looking.

              _“National City does not need Metropolis’ problems,”_ he was in the middle of saying.

              “Who cares what that guy says?” Winn told Kara.

              “You do,” she replied. “Isn’t Maxwell Lord your personal hero?”

              Winn looked up at the TV. “I own a couple Maxwell Lord watches and his biography. And his autobiography,” Winn said, trying to sound as casual as possible. Maxwell Lord fell under the category of Winn’s strangers he’d fallen in love with. Of course, it’s not like it was a particularly exclusive club. And Kara didn’t really need to know that.

              Kara’s demeanor changed as she straightened up. “She’s here,” she said.

              Winn looked over at her. “Well, at least now I know how you do _that_ ,” he said. _Super hearing. How cool is that?_

              Winn headed to his desk as Kara scurried off after Cat. He watched her go, before sitting down and getting ready for the various employees who didn’t know how computers worked coming to him with problems. It’s not that Winn didn’t like his job- he did- but he could do without the people claiming their computers were broken because they somehow didn’t know how to turn them on.

              Winn was just lucky he had as much patience as he did.

\---

              The next day at work, Winn was on his computer at his desk, continuing to avoid his new coworker, when Kara came up to him.

              “Meet me in alley in five minutes,” she said quickly before walking away.

              “Thank god you didn’t say the roof,” Winn replied as she left, mostly to himself.

              He finished up what he was working on as fast as he could before heading outside to wait for her, trying to look nonchalant. He didn’t want anyone asking where he was going.

              When he got outside, someone else was already in the alley. A tall, beautiful man. Winn just about died. He stopped walking, basically gawking at the man.

              “Hey, what’s up?” the man said, sounding hesitant.

              _Oh nothing, just on the brink of a panic attack._ “Nothing, nothing,” Winn said, sounding incredibly suspicious. “I like to come out here to… smoke.”

              The man crossed his arms over his chest, raising an eyebrow skeptically. Winn was ready to melt. Why did _he_ have to be here?

              “Which I like to do in private,” Winn continued, painfully unconvincingly. “So…”

              “Actually, I’m meeting someone right now,” the man said with a smile. He put a hand on Winn’s shoulder. Winn died.

              He tried to get ahold of himself. He was supposed to meet _Kara_ , he couldn’t get distracted right now. “Yeah, you can meet them inside the building. Yeah?”

              “No, uh, my friend like to make an entrance,” the man replied.

              Winn found himself looking up at Ridiculously Handsome Guy’s face. He was so much _taller_ than Winn. Winn felt his heart beat faster from being this close to him. He wasn’t sure what he was going to say- possibly _I’m in love with you, can we hang out-_ but then Kara landed dramatically in front of them.

              Winn was exhausted. He couldn’t deal with these people. They were too beautiful and he needed to only see them every three months or so because this was just overwhelming. He didn’t even know who to be fawning over. Who to be nervous about.

              This was going to be the death of him.

              Then it hit him. “He knows?” he asked Kara, surprised. The other man said the exact same thing.

              “You told him?” Winn asked.

              “James already knew,” Kara told Winn. She turned to James. “And Winn’s my friend.”

              Winn glanced over at the man next to him. At least he finally knew his name, and could stop referring to him as Ridiculously Handsome Guy in his mind. _James._ It almost made him miss Kara calling him her _friend,_ which always stung just a little bit.

              Of course, he was happy to be her friend. But it was just a reminder that she would never feel what he felt.

              He saw the way James was looking at Kara. It looked like James would never feel what he felt, either.

              Oh well. It’s not like Winn wasn’t used to pining.

              “If I’m going to be a hero, and prove to everyone that I know what I’m doing,” Kara started. “I’m gonna need to practice. Start small, get better. And to do that, I’m gonna need your help.”

              Winn was both excited and dismayed. Watching Kara be Supergirl was never going to help him get over her. Being in the same room at James was never going to help Winn get over _him._ He was going to have to get used to all the nerves and all the melting if he wanted to live out his childhood comic book dreams.

              “I’m in,” Winn said at the same time as James.

              Winn glanced at James, looked at him looking at Kara, looked at Kara looking at James. This was going to be interesting. And painful.

              Winn tried to emotionally prepare himself.

\---

              Kara went off while Winn and James stayed at her apartment, sending her locations to go after. Winn was almost able to get himself to stop stuttering, but he was painfully aware of James’ presence. Leaning a little too close while Winn sat at the computer.

              “Could you, uh, give me some space?” Winn asked, not quite breathing like a normal person.

              James put his hands up and backed off. “Sorry.”

              Winn glanced up at him, feeling his face get hot. This proximity wasn’t working for him. He was going to have to find a way to manage this, like he had with Kara. He couldn’t be spiraling in a panic around James all the time. Yes, he was beautiful, and yes, Winn just kind of wanted to tell him that every five seconds. But he was going to have to _chill._

              Which Winn had basically never done in his life. Maybe he had the right idea that other morning, hiding from James behind the wall to avoid being trapped in an elevator with him.

              He turned to James, putting on his best casual smile. He was sure the cartoon hearts circling his head gave away what he was feeling anyway. “Should we order food?”

              James smiled back. Winn died for the seventh time that day. “I could go for some pizza.”

              “Great,” Winn replied with a grin. _Something to distract me. Also, to put in my mouth to stop me from talking._ “What kind of pizza do you want? I’m fine with anything, unless you want pineapple on it- I don’t know how I feel about pineapple on pizza, you know? It just seems kind of wrong, but I mean, if-”

              “Plain cheese is fine,” James interrupted with a stiff smile.

              Winn crumpled a little. “Great,” he repeated, quieter. He smiled, a little too nervously. He rushed over to the phone, catching James shaking his head and chuckling out of the corner of his eye. At least his bumbling panic seemed to amuse James more than it annoyed him.

\---

              “ _Next?”_ Kara asked.

              James grabbed a slice of pizza from the box Winn was holding, shooting him a smile. Winn managed not to trip. “Ambulance caught in traffic on Donner Avenue carrying a heart attack victim,” James told Kara. “They’re not going to make it to Nation City General in time.”

              “Oh, and a fully loaded ambulance weighs about 9,200 pounds, which would mean that you’d need to use a maximum of 44,498 newtons of force-” Winn said, feeling himself ramble. He and James were both leaning over the computer. Winn was close enough to feel how warm James was. He was about to die. Again.

              “Kara,” James said, cutting Winn off. “What he means is- gently this time.”

              “I was getting to that,” Winn mumbled, his face getting hot.

              James shot him a wide smile. “Sure you were.”

              “I was _about_ to say it,” Winn said, crossing his arms.

              James shrugged. “Whatever you say.”

              Winn tried to hide his growing smile. He really, really liked that he and James were getting along well enough. He so wanted James to like him.

\---

              As they watched the news, Kara was practically bouncing from excitement. The media was being much kinder to her- praising her heroics. Winn was beaming.

              “I can’t believe it,” she said, grinning. She walked away from the television, over to where Winn and James were standing next to each other. “It’s working. People are really starting to believe in her.”  

              “In _you,”_ James corrected. Winn looked up at him, at his beautiful smile and warm eyes. It was such a nice thing to say. Winn was having a hard time even bothering to _try_ to not fall for him. It was a hopeless cause.

              “I couldn’t have done it without you,” Kara replied kindly, gazing back and forth between Winn and James. Her eyes seemed to settle more on James. At least, Winn didn’t think he was imagining it. “Thank you. Both of you.”

              Winn noticed she added that last part almost as an afterthought. He glanced back at James. How could he not notice how they were looking at one another? He pushed the thought away, convincing himself to put off dwelling and obsessing until he was at home. He could bask in this moment for now.

              The moment didn’t last much longer. Kara’s sister got there, and Winn could feel the room get tenser. It became clear that Kara needed to talk to her sister alone. Winn and James both fumbled with words for a moment before leaving, a little rushed.

              Winn didn’t say anything as they left the building, feeling his heart beat faster. James didn’t say anything either.

              They got to the sidewalk, lingering for an awkward few moments. Winn didn’t know where to begin. He managed to barely stop himself from saying _You’re amazing and also really handsome, please come get dinner with me._ It wasn’t even dinnertime. They’d already had dinner.

              James inhaled, patting Winn quickly on the shoulder. “Well. That was fun,” he said, smiling.

              Winn melted. “Yeah,” he said, smiling back. He felt a little dazed and dreamy. He snapped himself out of it as fast as he could, clearing his throat. “Yep, um, it was, uh, great. Hopefully, we can do it again sometime. I mean. With Kara. Obviously.”

              James chuckled. “Right.”

              He looked uncomfortable. Winn didn’t blame him. He wouldn’t be sure how to deal with his stammering either. “Well, anyway,” Winn said, rubbing the back of his neck nervously. “It was, ah, good. Yeah. I’ll, um, see you at work.”

              He spun around and walked away briskly. It took him three blocks to realize he was going the wrong direction.


End file.
